When I launched my MVP, Insurance by Jack, in 2014 I struggled to win sales.

One week passed… nothing. Week two… zilch.

It took me three weeks to make my first sale. It was a slither of momentum, but it wasn’t the start of my business gaining steam.

I knew why I was struggling. Insurance by Jack had a strong brand, but the process of getting a quote involved sending potential customers to a third-party. This resulted in a customer journey that wasn’t cohesive and made for a poor user experience.

Fast forward two years, Insurance by Jack has evolved into With Jack and I’ve been granted more permission and responsibility. Now that I’ve taken control of the design and technology, I’ve created a customer journey that compliments With Jack’s brand.

The theory that this would improve sales was true. So much so, I made my first sale three weeks before I launched. A stark contrast to 2014’s launch to crickets.

Last week I celebrated putting my 50th freelancer on cover, but I want to start at the beginning and share how I won my first three customers.

My First Customer

In the run up to launch, I replaced Insurance by Jack’s website with a landing page. I wrote a couple of paragraphs on my vision for insurance, which I followed with a call to action to be notified of launch.

Jack's landing page
The landing page that replaced the original website

120+ people opted in. This surprised me because it’s insurance. Having 10 people pay attention would have been a success.

I sent 3 emails to this list.

1. Coming soon: The new Jack. I touched upon my journey in insurance and detailed what people can expect from the new Jack.

2. Want to test the new Jack? A short email asking for beta testers. 29 people responded.

3. Introducing the new Jack. The soft launch email. I announced I was open for business.

Designers and developers love collaborating. They enjoy seeing other people’s work and offering solutions as to how they’d approach it differently.

Email number 2—where I asked people to test the quote form—was the ideal way to open dialogue with my target audience. Not only did I get constructive feedback on the process, but several people actually wanted to buy insurance.

This is how I won my first customer before I launched.

Lesson: Involve your target audience in the build process. At the very least be transparent about what you’re working on—people will take an interest and want to support you.

My Second Customer

I quietly pushed With Jack live from a hotel room in Berlin with terrible WIFI.

When I say quietly, I didn’t announce the service was available. I deployed it to GitHub Pages, walked away and played tourist in Berlin.

The following day I checked my CRM tool and was surprised to see a quote had come through. It was from a name I recognised.

This person had been following me on Twitter for years. Our first exchange was 5 years ago—back in 2012! This was two years before I had even started my crusade into business insurance.

Lesson: Marketing is about playing the long game. Relationships established years ago may blossom into paying customers.

My Third Customer

By this point I still hadn’t announced I’d launched With Jack. I was aiming to do a few weeks in soft launch mode, so I was expecting any quotes that came through to be from beta testers.

During this time I gave a talk at Hybrid, a conference for creatives.

With the first iteration of With Jack (Insurance by Jack), I had no control over the customer journey. I had no idea who my customers were or where they were coming from. It made tracking marketing very difficult. Especially public speaking.

As a quote had come through from someone that wasn’t a beta tester, I asked where they’d heard of Jack.

We heard about Jack through friends that'd been chilling at Hybrid. We looked at your site and we're suckers for a good design. Truth be told we'd never thought about insurance, but the site was fun, friendly and didn't feel like chewing glass.

What do you know, public speaking can convert. Thanks to the HybridConf attendee who passed along With Jack’s name.

Lesson: Share your story everywhere. All it takes is for one person to hear it and tell their friends.


I won my first three customers through the following channels:

  • Beta tester
  • Twitter
  • Public speaking

I’m having a lot of fun building With Jack and finding ways to win customers, but I do need a better formula.

I’m heading to Switzerland for my birthday in a few weeks for a (working) holiday. One of the books I plan on reading is Traction. I’m hoping to use their three-step framework to discover the best channels for marketing With Jack.

Hopefully one day I’ll be writing about winning my 3000th customer, but I’m documenting my journey of building an insurance business from the start.